All you need to know about the Paypal Mafia

Background

Vaibhav Bajaj
10 min readMay 7, 2021

Do you know what is common among the list of companies below?

Youtube, Linkedin, Tesla, SpaceX, Yelp, Yammer, Palantir Technologies, Affirm, Kiva.

They were all founded by The Paypal Mafia. The term was coined for former Paypal founders and employees who after leaving Paypal founded some of the biggest tech companies in the world as you can see in the list above. At some point, most of them had either attended Stanford or the University of Illinois, Urbana Champaign for their studies.

Members of the PayPal Mafia on Fortune magazine dressed in mafia-like attire. From left to right, top to bottom: Jawed Karim, Jeremy Stoppelman, Andrew McCormack, Premal Shah, Luke Nosek, Ken Howery, David O. Sacks, Peter Thiel, Keith Rabois, Reid Hoffman, Max Levchin, Roelof Botha, Russel Simmons. Image Courtesy: Wikipedia

In this blog, you will find:

  • The people who are part of the Mafia
  • What they did/are doing after leaving Paypal
  • Succinct details about them
  • What are the things that I find interesting about some of them
  • Their net worth

FYI… For some of the members, there isn't much information present on the vast web.

Who are the members of this said Paypal Mafia?

  • Peter Thiel
“Peter Thiel” by jdlasica is licensed under CC BY 2.0

Peter Thiel was the co-founder and CEO of PayPal. He was referred to as the “Don” of the PayPal Mafia. He earned $55M after selling PayPal to eBay and was also the first outside investor of Facebook.

He is currently the co-founder of Palantir Technologies and Founder’s Fund. His company Palantir Technologies works with the US Government, military, intelligence, and police.

I have a favorite quote from Peter Thiel:

We wanted flying cars, instead we got 140 characters;

Famously, he backed Bollea in the Bollea vs Gawker lawsuit, which eventually caused the bankruptcy of Gawker.

You are wondering why the above statement was relevant and necessary. He backed Bollea because Gawker had previously outed him as gay. Ohh by the way, you might not recognize Bollea. Remember Hulk Hogan. Bollea is Hulk Hogan.

Moreover, he also supported and financed Donald Trump’s campaign.

His net worth is over $2B.

  • Max Levchin
“PayPal Co-Founder Max Levchin, Allen & Company, 2015” by Thomas Hawk is licensed under CC BY-NC 2.0

Max Levchin was also the co-founder of PayPal and the CTO. He was called the “consigliere” of the PayPal Mafia. Levchin made $34M from the sale to eBay and then founded Slide and Affirm. He sold Slide to Google in 2010 for $180M.

Levchin is also famous for his contributions to Paypal’s anti-fraud efforts and made one of the first commercial applications of CAPTCHA.

CAPTCHA: Completely Automate Pubilc Turing test to tell Computers and Humans Apart.

Levchin was an early investor in Yelp and was the chairman of the board of directors, until 2015. In 2015, he also established Levchin prize which annually provides 2 awards of $10,000 to people or groups who provide significant contributions to real-world cryptography.

His net worth is $1B+.

  • Elon Musk

Elon Musk, better known as the crazy centi billionaire who is going to take us to Mars. You might also know him from his tweets which usually take Cryptos to the moon(Dogecoin, IYKYK).

Elon Musk was the founder of X.com. In 1999, he merged his company with a venture-backed competitor Confinity(Thiel and Levchin), and was named CEO and the largest shareholder.

During the fall of 2000, Thiel and Levchin staged a coup and fired Elon from the company when he returned after a two-week meeting with potential investors. Thiel was named CEO and the company was rebranded as PayPal.

When PayPal went public and got acquired by eBay, Elon made ~$165M, ~5X of what Levchin or Thiel made individually.

He now runs the following companies simultaneously while allegedly trying to smoking pot on Joe Rogan’s podcast; Tesla, SpaceX, The Boring Company, Neuralink, and OpenAI.

His net worth: $160B+.

  • David Oliver Sacks
Image: https://commons.wikimedia.org/wiki/File:David_O._Sacks.jpg

After leaving McKinsey & Company, David joined PayPal as their COO and product leader. After PayPal, David produced and financed the hit movie ‘Thank You For Smoking’.

He also founded Geni.com which spun into the social network Yammer, which was acquired by Microsoft for $1.2B in 2012.

Moreover, he is an angel investor in a bunch of companies such as OpenDoor, PostMates, Facebook, Scribd, Slack, Palantir, Affirm, Airbnb, etc.

He also co-founded Craft Ventures, a VC, and invested in companies such as Bird, BitGo, SpaceX to name a few.

Ohh by the way, he threw a 40th birthday bash with the theme “Let them eat cake” that included the likes of Snoop Dogg after the acquisition of Yammer by Microsoft. The party was hosted at Fleur de Lys mansion in Beverly Hills. The entire party cost David, $1.2M for the night, which was one-tenth of 1 percent of what Microsoft paid to acquire Yammer.

His net worth is Unknown.

  • Steve Chen
Image: https://commons.wikimedia.org/wiki/File:YouTube_TaiwanVersionLaunch_SteveChen-2.jpg

Steve Chen joined PayPal as a top engineer. There he met Jawed Karim and Chad Hurley and later founded Youtube, and became the Chief Technology Officer. When Google acquired Youtube, he got ~700k google shares which are now worth more than ~$2B. He joined Google Ventures in 2014. In March 2019 he became an advisor to Theta, a peer-to-peer video streaming network that uses blockchain technology.

His estimated net worth is $300M+.

  • Reid Hoffman
Image: https://commons.wikimedia.org/wiki/File:Reid_Hoffman_in_SF_2011.jpg

Before PayPal, Reid Hoffman had already begun SocialNet.com which used to match people with similar interests. Peter Thiel himself said that SocialNet.com was

literally an idea before its time. It was a social network 7 or 8 years before that became a trend.

Reid first joined PayPal as their COO in 2000 after quitting SocialNet, though he was already on the board of directors during the founding of PayPal. At PayPal, he used to handle all external communications and was colloquially called the firefighter-in-chief of PayPal. After the sale to eBay, he became the EVP.

He later co-founded LinkedIn in 2002. His shares in LinkedIn are worth well over $2B and when Microsoft acquired Linkedin, he joined the board of Microsoft.

Reid has also been an angel investor in over 80 companies such as Airbnb, Blockstream, Coda, etc.

Fun Fact: He was the one who arranged the first meeting between Mark Zuckerberg and Peter Thiel, which led to Thiel’s $500k angel investment in Facebook.

His net worth is $4B+.

  • Ken Howrey
Image: https://commons.wikimedia.org/wiki/File:Ken_Howery.jpg

Ken was a co-founder and COO for PayPal from 1998–2002.

He started Founders Fund in 2005 with “pals” Thiel and Nosek. The portfolio for Founders Fund includes Lyft, Airbnb, Spotify, Stripe, etc.

He has also served as the US Ambassador to the kingdom of Sweden from 2019- 2021 during the Trump Administration.

His net worth is $1.5B+.

  • Chad Hurley
Image: https://commons.wikimedia.org/wiki/File:Chad_Hurley_-World_Economic_Forum_Annual_Meeting_Davos_2007.jpg

Chad Hurley joined the PayPal team as their web designer. He was the one who was responsible for designing the original PayPal logo.

After leaving PayPal, Chad, Steve, and Jawed founded Youtube in 2005. They sold Youtube to Google in 2006 for $1.6B. He received more than 730k shares which were worth~$350M in February 2007. During that time, he was primarily responsible for tagging and video sharing aspects for Youtube.

He is an American webmaster and also part-owner in NBA’s Golden State Warriors, MLS’s Los Angeles Football Club. This year, he became an investor in Leeds United, a team in the English Premier League.

His net worth is $350M+.

  • Eric M Jackson
Image: https://ericmjackson.wordpress.com/about/

Eric was the marketing executive at PayPal who went on to write the book “The PayPal Wars”. After PayPal, he became chief executive officer of WND Books and co-founded CapLinked.

He is well known for his conspiracy and controversial theories and statements respectively.

His net worth is unknown.

  • Jawed Karim
Image: https://en.wikipedia.org/wiki/Jawed_Karim#/media/File:Jawed_Karim_2008.jpg

Jawed joined PayPal as an engineer. He created their anti-fraud system. After the sale, he joined forces with Chad Hurley and Steve Chen to launch Youtube.

After launching Youtube, Jawed enrolled in the Computer Science course at Stanford in 2005, thus acting only as an informal adviser to Youtube. He thus took a lower stake in the company and stayed relatively unknown until Youtube was acquired by Google.

By the way, he uploaded the first video on Youtube, Me at the zoo which has more than 160M views as of now.

Moreover, he was one of the factors that led Google to drop the idea of Google+, after he supported the youtube community in their stand against using Google+ to comment on youtube videos.

Karim launched Youniversity Ventures in 2008 to help students develop business ideas.

His net worth is $140M.

  • Jared Kopf

Jared was Peter Thiel’s executive assistant. After leaving PayPal, Jared co-founded Slide, HomeRun, and NextRoll. He has made over 60 investments and now serves as Chairman of AdRoll.

His net worth is unknown.

  • Joe Lonsdale
Image: https://8vc.com/team/joe-lonsdale/

Joe started as a finance intern at PayPal before moving into venture capital. Since PayPal, he’s worked at VC firms Clarium Capital, Formation 8, and 8VC. By the way, Lonsdale also co-founded Palantir.

His net worth is $400M+.

  • Dave McClure
Image: https://commons.wikimedia.org/wiki/File:Dave_McClure_2007.jpg

Dave McClure was PayPal’s director of marketing for 4 years. He left PayPal in 2004. After PayPal, he had a small run at Founders Fund before launching 500 Startups. He has also invested in 500+ startups.

Dave was involved in the AngelGate controversy in 2010.

His net worth is $5M+.

  • Andrew McCormack
Image: Twitter

Andrew joined PayPal in 2001. He worked closely as Peter Thiel’s assistant as they prepped to IPO. After Paypal, he helped launch hedge fund company Clarium Capita with Peter Thiel. He and Peter Thiel also founded Valar Ventures together.

His net worth is unknown.

  • Luke Nosek
Image: https://commons.wikimedia.org/wiki/File:Luke_Nosek_(8518034389).jpg

Luke Nosek co-founded PayPal and was the former vice president of marketing and strategy. He created the company’s instant transfer product. After PayPal, he became a partner at Founders Fund with Peter Thiel and Ken Howery.

In his first conversation with Thiel, he told Thiel that he had registered to be cryonically suspended. In other words, he would be subject to low-temperature preservation, in case of his legal death in hopes that he might be successfully revived by future medical technology. Surprisingly, Thiel followed Nosek’s example to be cryonically suspended.

He is the first institutional investor to Elon Musk’s SpaceX and sits on the company’s board.

His net worth is unknown.

  • Keith Rabois
Image: https://www.flickr.com/photos/techcrunch/5759368240

Keith was a former executive at PayPal. He later worked at LinkedIn as VP of business and corporate development.

He has also worked in Slide, Square, and Khosla Ventures. He cofounded OpenDoor in 2014.

He is well known for his early investments such as Yelp and Xoom and sits on both the company’s board of directors.

He rejoined Peter Thiel at Founders Fund as a General Partner in 2019.

His estimated net worth is $1B+.

  • Russel Simmons
Image: https://www.flickr.com/photos/joeywan/324687443. Megan McCarthy (Valleywag) and Russel Simmons (Yelp Co-founder/CTO)

Russel was PayPal’s Lead Software Architect. After PayPal, he joined forces with Jeremy Stoppelman to co-found Yelp. He left Yelp in 2010 and founded Learnirvana in 2014.

His net worth is unknown.

  • Jeremy Stoppleman
Image: https://commons.wikimedia.org/wiki/File:Jeremy_Stoppelman_LeWeb_conference.jpg

Jeremy joined PayPal as an engineer while it was still known as X.com. Jeremy eventually became the Vice President of Engineering. After the eBay sale, Jeremy joined Russel Simmons to launch Yelp.

His net worth is $150M+.

  • Yishan Wong Yishan
Image: Twitter

Yishan Wong Yishan was the former engineering manager at PayPal. In 2005, he joined Facebook as a director of engineering. After leaving Facebook, he became the CEO of Reddit in 2012. He decided to step down in 2014 after having a disagreement with the board members for moving the Reddit Office from San Fransisco to Daly city as he thought that the employees would prefer working from a less expensive area.

He is the co-founder of Sunfire Offices and an advisor to Quora. He also is a contributing editor to the Forbes Magazine since 2011.

In 2020, he founded Terraformation, a global forest accelerator with a mission to reverse climate change by unlocking global reforestation.

Hope you enjoyed this detailed blog. Let me know if you have any feedback :)

References:

  1. https://en.wikipedia.org/wiki/PayPal_Mafia. All the connecting pages for all the individual members on Wikipedia were also referred.
  2. https://www.businessinsider.in/tech/meet-the-paypal-mafia-the-richest-group-of-men-in-silicon-valley/articleshow/43010046.cms
  3. https://www.scmp.com/magazines/style/celebrity/article/3107043/tesla-and-spacex-billionaire-founder-elon-musk-was-fired
  4. https://fleximize.com/paypal-mafia/
  5. https://www.businessinsider.com/snoop-dogg-david-sacks-yammer-photo-2012-6?IR=T

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Vaibhav Bajaj

An ardent data, product and sports enthusiast with a knack for problem-solving and constant humor. Also, creating content because I want to ;). WhiteClay :)